Réaction #833521

Équation de réaction

THF

4a

1,4-dimethoxy-6,7,10,11-tetrakis(decyloxy)triphenylene

→

5a

Rendement 80.0%

6,7,10,11-tetrakis(decyloxy)triphenylene-1,4-dione

Rendement 80.0%

Solvants

ether

Conditions de réaction

Traitement

1. 1
   Lavagewashed with a saturated solution of NaHCO3 and water
2. 2
   SéchageThe organic layer was dried with MgSO4
3. 3
   Autrethe solvent removed under reduced pressure
4. 4
   AutreThe crude product was purified by column chromatography on silica gel (1:1 CH2Cl2/hexane)

Mode opératoire

An aqueous solution (1 mL) of (NH4)2Ce(NO3)6 (0.035 g, 0.064 mmol) was added dropwise to a THF solution (5 mL) of 4a (0.029 g, 0.032 mmol). The reaction mixture immediately turned deep red. After 6 h the reaction mixture was poured into ether and washed with a saturated solution of NaHCO3 and water. The organic layer was dried with MgSO4 and the solvent removed under reduced pressure. The crude product was purified by column chromatography on silica gel (1:1 CH2Cl2/hexane) to afford 5a as a deep red solid in 80% yield (mp 86-87° C.).

Source